Montagano was an associate at the law firm of Stuart & Branigin LLP in Indianapolis before becoming the Democratic nominee for the U.S. House of Representatives in Indiana's Third District during the 2008 election and later serving as in-house counsel for a local mid-sized business. Montagano has served several Hoosier leaders in various capacities, including Indiana Gov. Joe Kernan, U.S. Rep. Tim Roemer, D-Indiana, and U.S. Rep. Joe Donnelly, D-Indiana. He has joined Baker & Daniels LLP as an associate in the business and corporate finance practice in the firm's South Bend office Montagano graduated cum laude from both DePauw University in 2003 and Indiana University School of Law-Indianapolis in 2006.